Method for synthesizing florfenicol

A technology of florfenicol and synthetic method, which is applied in the field of florfenicol synthesis, can solve the problems of low conversion rate, many by-products, rising synthesis cost, etc.

Inactive Publication Date: 2008-09-17
SHANGHAI RECORD PHARM CO LTD
View PDF3 Cites 26 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Due to the asymmetry of the chiral functional groups in the above route, chiral resolution is required, resulting in many by-products and low conversion rates during the synthesis process, which leads to an increase in synthesis costs

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for synthesizing florfenicol
  • Method for synthesizing florfenicol
  • Method for synthesizing florfenicol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0058] How to implement the present invention will be further described below in conjunction with specific examples. The following examples are helpful for understanding the present invention, but are not limited to the content of the present invention.

[0059] (A) compound 1 is protected by protecting group to prepare compound 2

[0060] Dissolve 5 g of L-threo-[p-(thysulfonyl)phenyl]serine ethyl ester in 10 ml of methanol and 30 ml of dichloromethane, and cool to 10° C. in an ice bath. Mix benzoyl chloride with 2.2ml of dichloromethane and add it dropwise into the reaction flask, control the temperature not higher than 20°C, stir at room temperature for 2 hours, add 2.7g of thionyl chloride, and react compound 1 with benzoyl chloride The reaction was carried out at a ratio of 1:1.5. The reaction system was heated to 50° C. and kept at this temperature for 2 hours, then naturally cooled to room temperature, added 30 g of ice water, stirred for 30 minutes, and stood to separa...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses a synthesis method of synthesizing florfenicol. The synthesis method comprises the following steps: L-threo-(p-(methylsylfonyl) phenyl) serine ethyl ester which is used as raw material is processed by the protection by a protecting group, configurational transition, hydrolyzation, acetylation, re-protection, deoxidation, fluorination, and pre-hydrolyzation, so that the florfenicol is obtained, wherein, the protecting group R is one of benzoyl chloride, phthalic anhydride, cyanophenyl, and allyl compounds; the configurational transition is performed when sodium alcoholate or sodium methoxide exists. The raw material which is used in the method is a byproduct which is generated during the process of preparing thiamphenicol, is easy to get in the market, and is inexpensive; the technological operation is simple, the cost is low, the yield rate is high, and the synthesis method has industrialized value.

Description

technical field [0001] The invention relates to a synthetic method of florfenicol. Background technique [0002] Florfenicol is a broad-spectrum antibiotic of the chloramphenicol class. Florfenicol (Florfenicol) is also known as fluthiamphenicol, clofenacil. Florfenicol was registered by the US FDA in 1996. It is a new type of anti-Gram-positive bacteria specially developed for the animal health market. It is a broad-spectrum antibacterial drug for animals. Its structure is similar to thiamphenicol, but its antibacterial ability Up to 10 times as much as thiamphenicol, so it is widely used. [0003] Florfenicol is generally synthesized from the intermediate D-(-)-2-amino-1-[(p-thiamphenicol)phenyl]-1,3-propanediol of thiamphenicol (US4235892, US4311897, Tetrahedron Lett, 1988.29(43).5561-5564), the reaction scheme is as follows: [0004] [0005] Due to the asymmetry of chiral functional groups in the above route, chiral resolution is required, resulting in many by-pr...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/32C07C315/04A61P31/04
CPCY02P20/55
Inventor 张芳江
Owner SHANGHAI RECORD PHARM CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap